Nova Patents
US8445481B2

Scaffold-diversified pyrrolidinone derivatives and their use

Claim Score by NHIP

Read claim 14, the broadest

Abstract

The present disclosure provides novel compounds of the formula (I): wherein R0, R1, R2, R3, R4, R5, and R6 are as defined in the detailed description. Two preferred compounds of formulae (IX) and (X) are disclosed. Also disclosed are uses of the disclosed compounds, for example, in regulating glucose transport and in inhibiting acetyl coenzyme A carboxylase.

US8445481B2, drawing sheet 1
Sheet 1 of 69

Term

Projected expiry 2 February 2029.

  1. Priority
  2. Filed
  3. Granted
  4. Today
  5. Projected expiry

18 claims: 3 independent, 15 dependent

  1. 1
    A compound of the formula (II):or a pharmaceutically acceptable salt thereof, where R 0 is hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, —OR′, —OC(O)R′, —OC(O)NR′R″, —NR′C(O)R″, —NR′C(O)NR″R′″, —NR′R″, —NR′CO 2 R″, —NR′S(O) 2 R″, —SR′, —S(O)R′, —S(O) 2 R′, —S(O) 2 NR′R″, or C 6-10 aryl, where R 3 is hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, —NR′C(O)R″, —NR′C(O)NR″R′″, —NR′R″, —NR′CO 2 R″, —NR′S(O) 2 R″, or C 6-10 aryl, where R 4 , R 5 , and R 6 are each independently hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, or C 6-10 aryl, and R 5 and R 6 may, together with the atoms to which they are attached, form a 3- to 10-membered ring, where Z is carbon, nitrogen, oxygen, or sulfur, where n is 0-3, where R 7 can substitute any open valence of any ring within the structure, and R 7 is hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, —C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, —OR′, —OC(O)R′, —OC(O)NR′R″, —NR′C(O)R″, —NR′C(O)NR″R′″, —NR′R″, —NR′CO 2 R″, —NR′S(O) 2 R″, —SR′, —S(O)R′, —S(O) 2 R′, —S(O) 2 NR′R″, C 6-10 aryl, and where R′, R″ and R′″ are each independently selected from the group consisting of hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl;and R′ and R″ or R″ and R′″ may, together with the atoms to which they are attached, form a 3- to 10-membered ring.
  2. 10
    A compound of the formula (VIa):or a pharmaceutically acceptable salt thereof, where R 0 is hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, —OR′, —OC(O)R′, —OC(O)NR′R″, —NR′C(O)R″, —NR′C(O)NR″R′″, —NR′R″, —NR′CO 2 R″, —NR′S(O) 2 R″, —SR′, —S(O)R′, —S(O) 2 R′, —S(O) 2 NR′R″, or C 6-10 aryl, where R 3 is hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, —NR′C(O)R″, —NR′C(O)NR″R′″, —NR′R″, —NR′CO 2 R″, —NR′S(O) 2 R″, or C 6-10 aryl, where R 5 , and R 6 are each independently hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, or C 6-10 aryl, and R 5 and R 6 may, together with the atoms to which they are attached, form a 3- to 10-membered ring, where Z is carbon, nitrogen, oxygen, or sulfur, where n is 0-3, where R 7 can substitute any open valence of any ring within the structure, and R 7 is hydrogen, halogen, C 1-20 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, —CN, —NO 2 , —C(O)R′, —CO 2 R′, —C(O)NR′R″, —OR′, —OC(O)R′, —OC(O)NR′R″, —NR′C(O)R″, —NR′C(O)NR″R′″, —NR′R″, —NR′CO 2 R″, —NR′S(O) 2 R″, —SR′, —S(O)R′, —S(O) 2 R′, —S(O) 2 NR′R″, C 6-10 aryl, and where R′, R″ and R′″ are each independently selected from the group consisting of hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 6-10 aryl, 5- to 10-membered heteroaryl, and 3- to 10-membered heterocyclyl;and R′ and R″ or R″ and R′″ may, together with the atoms to which they are attached, form a 3- to 10-membered ring.
  3. 14
    Broadest claimClaim Score 98, very broad(NHIP)A compound of the formula (X):or a pharmaceutically acceptable salt thereof.
Independent claims3